2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS No.: 496052-68-7
• Molecular Formula: C₅₀H₅₅NO₁₂Si
• Molecular Weight: 890.072

Synonyms:2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chemical Property of 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chemical Property:

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Technology Process of 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

There total 4 articles about 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (496052-66-5) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (496052-68-7)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0040-4039(02)01947-0

Reference yield:

tert-butyldiphenylsilyl 2-phthalimido-3,6-di-O-benzyl-2-deoxy-β-D-dlucopyranoside → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (496052-68-7)

Guidance literature:

Multi-step reaction with 2 steps

1: AgOTf / 1,2-dichloro-ethane / -15 °C

2: NaOMe / methanol / 1 h / 20 °C

With sodium methylate; silver trifluoromethanesulfonate; In methanol; 1,2-dichloro-ethane;

DOI:10.1016/j.tet.2003.08.047

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (496052-68-7)

Guidance literature:

Multi-step reaction with 2 steps

1: AgOTf / 1,2-dichloro-ethane / -15 °C

2: NaOMe / methanol / 1 h / 20 °C

With sodium methylate; silver trifluoromethanesulfonate; In methanol; 1,2-dichloro-ethane;

DOI:10.1016/j.tet.2003.08.047

upstream raw materials:

tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

acetic acid 6-acetoxy-5-acetoxymethyl-2-[4-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

tert-butyldiphenylsilyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

C₅₃H₅₉NO₁₂Si

N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-hydroxy-tetrahydro-pyran-3-yl]-2,2,2-trichloro-acetamide

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